Cyanoguanidine as a versatile, eco-friendly and inexpensive reagent for the synthesis of 2-aminobenzoxazoles and 2-guanidinobenzoxazoles. Issue 17 (25th April 2018)

• Record Type: Journal Article
• Authors: Grytsai, Oleksandr; Druzhenko, Tetiana; Demange, Luc; Ronco, Cyril; Benhida, Rachid
• Is Part Of: Tetrahedron letters. Volume 59:Issue 17(2018)
• Page Start: 1642
• Page End: 1645
• Publication Date: 2018-04-25
• Subjects: 2-Aminobenzoxazole -- 2-Guanidinobenzoxazole -- Cyclocondensation -- Lewis acid activation; JPBLHOJFMBOCAF-UHFFFAOYSA-N -- QHVCONQZXJPGQZ-UHFFFAOYSA-N -- UHYVXILHAMUPRP-UHFFFAOYSA-N -- WQIUYAJFFXBLGX-UHFFFAOYSA-N -- QDMXVLGVKMTTIT-UHFFFAOYSA-N -- YGCODSQDUUUKIV-UHFFFAOYSA-N -- DQUOOHJLHOWIHQ-UHFFFAOYSA-N -- FNGZREDJXWXRBW-UHFFFAOYSA-N -- NIFGELXGXJWBEK-UHFFFAOYSA-N -- KDQALQJUSXAKQK-UHFFFAOYSA-N -- IHJJJTGOBJCCHQ-UHFFFAOYSA-N -- JKWBBBHWLUOBPY-UHFFFAOYSA-N -- GBKJNSTZJIUTER-UHFFFAOYSA-N -- XUMGOFYFGJULSA-UHFFFAOYSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.03.036
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Under specific Lewis acid activation, cyanoguanidine acts as cyanating agent. Cyanoguanidine/BF3 allows safe and eco-friendly synthesis of 2-aminobenzoxazoles. AlCl3 activation broadens and optimizes the synthesis of 2-guanidinobenzoxazoles. Abstract: An effective, easy-to-handle, safe and inexpensive protocol is reported for the synthesis of 2-aminobenzoxazoles under Lewis acid activation, utilising cyanoguanidine as the cyanating reagent. An optimized procedure for the synthesis of 2-guanidinobenzoxazole and novel derivatives is also described.